EP2960291B1 - Crosslinking aid and practical application thereof - Google Patents

Crosslinking aid and practical application thereof Download PDF

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Publication number
EP2960291B1
EP2960291B1 EP14753580.1A EP14753580A EP2960291B1 EP 2960291 B1 EP2960291 B1 EP 2960291B1 EP 14753580 A EP14753580 A EP 14753580A EP 2960291 B1 EP2960291 B1 EP 2960291B1
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EP
European Patent Office
Prior art keywords
meth
acrylate
crosslinking
crosslinking aid
ethylene
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
EP14753580.1A
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German (de)
English (en)
French (fr)
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EP2960291A1 (en
EP2960291A4 (en
Inventor
Mabuko Yamaura
Yukio Orikasa
Kazuya Senzaki
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Mitsubishi Chemical Corp
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Mitsubishi Chemical Corp
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Publication of EP2960291A1 publication Critical patent/EP2960291A1/en
Publication of EP2960291A4 publication Critical patent/EP2960291A4/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
    • C09J123/26—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers modified by chemical after-treatment
    • C09J123/36—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers modified by chemical after-treatment by reaction with compounds containing nitrogen, e.g. by nitration
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/20—Carboxylic acid amides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477—Six-membered rings
    • C08K5/3492—Triazines
    • C08K5/34924—Triazines containing cyanurate groups; Tautomers thereof
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
    • H01L31/04—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof adapted as photovoltaic [PV] conversion devices
    • H01L31/042—PV modules or arrays of single PV cells
    • H01L31/048—Encapsulation of modules
    • H01L31/0481—Encapsulation of modules characterised by the composition of the encapsulation material
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2331/00—Characterised by the use of copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, or carbonic acid, or of a haloformic acid
    • C08J2331/02—Characterised by the use of omopolymers or copolymers of esters of monocarboxylic acids
    • C08J2331/04—Homopolymers or copolymers of vinyl acetate
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
    • C09J123/02—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
    • C09J123/04—Homopolymers or copolymers of ethene
    • C09J123/08—Copolymers of ethene
    • C09J123/0846—Copolymers of ethene with unsaturated hydrocarbons containing other atoms than carbon or hydrogen atoms
    • C09J123/0853—Vinylacetate
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy

Definitions

  • the present invention relates to applications of a crosslinking aid. More specifically, the present invention relates to applications of a widely used crosslinking aid comprising triallyl isocyanurate (TAIC) (for example, a sealing material for a solar cell, etc.).
  • TAIC triallyl isocyanurate
  • Patent Literature 1 a resin composition comprising an ethylene-based copolymer as a base material and an organic peroxide as a crosslinking agent mixed with the ethylene-based copolymer.
  • an adhesive sheet for a solar cell which is constituted of 100 parts by weight of an ethylene-based copolymer and 0.05 to 0.5 parts by weight of an organic peroxide, and comprises a multifunctional monomer having four or more acryloyl and/or methacryloyl groups in total (Patent Literature 2).
  • a sealing film for a solar cell which comprises an ethylene-unsaturated ester copolymer, a crosslinking agent and a crosslinking aid, in which the crosslinking aid comprises a polyfunctional (meth)acrylate of a polyhydric alcohol and TAIC (Patent Literature 3).
  • TAIC is known as a useful crosslinking aid upon obtaining a molded body by curing a cross-linkable polymer.
  • TAIC when crosslinking an ethylene-based vinyl acetate copolymer with an organic peroxide, TAIC is essentially required as a crosslinking aid, and is capable of providing a sealing material for a solar cell which has high transparency, adhesive properties, heat resistance and flexibility.
  • a polymer having a polar group such as an ethylene-vinyl acetate copolymer tends to be insufficient in insulation properties (volume resistivity value) even when cross-linked using TAIC.
  • a polyfunctional (meth)acrylate of a polyhydric alcohol according to the above-proposed conventional art.
  • the present invention has been made in view of the above circumstances.
  • the object of the present invention is to provide a crosslinking aid comprising TAIC, which serves for obtaining an adhesive resin composition exhibiting excellent insulation properties while maintaining good transparency, adhesive properties, heat resistance and flexibility of conventional crosslinked ethylene-vinyl acetate copolymers.
  • the above object of the present invention can be achieved by using a specific compound in combination with TAIC.
  • the present invention has been accomplished on the basis of the above findings, and includes the following aspects relating to a crosslinking aid and applications thereof.
  • a crosslinking aid that is capable of providing an adhesive resin composition having excellent insulation properties while maintaining good transparency, adhesive properties, heat resistance and flexibility of conventional crosslinked ethylene-vinyl acetate copolymers.
  • the crosslinking aid used in the present invention comprises a urethane poly(meth)acrylate in combination with TAIC.
  • the urethane poly(meth)acrylate can be synthesized, for example, from an organic isocyanate and a hydroxyl group-containing (meth)acrylate.
  • the urethane poly(meth)acrylate having a high molecular weight is preferred.
  • the number-average molecular weight of the urethane poly(meth)acrylate is not less than 1000, and preferably not less than 1200.
  • the upper limit of the number-average molecular weight of the urethane poly(meth)acrylate is usually 10,000.
  • the organic isocyanate is a compound having two or more isocyanate groups in a molecule thereof.
  • the organic group include a linear, branched or cyclic aliphatic hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic ring group such as isocyanurate group.
  • Specific examples of the organic isocyanate include 1,6-hexamethylene diisocyanate, isophorone diisocyanate, toluidine diisocyanate, MDI (diphenylmethane diisocyanate), hydrogenated MDI, xylylene diisocyanate, a trimer of 1,6-hexamethylene diisocyanate, and a trimer of isophorone diisocyanate.
  • the hydroxyl group-containing (meth)acrylate is a (meth)acrylate having one or more hydroxyl groups in a molecule thereof.
  • Examples of the hydroxyl group-containing (meth)acrylate include (meth)acrylates of polyhydric alcohols.
  • hydroxyl group-containing (meth)acrylate examples include trimethylolpropane di(meth)acrylate, pentaerythritol trimethacrylate, dipentaerythritol tetra(meth)acrylate, tripentaerythritol (meth)acrylate, polyalkyl diol (meth)acrylates, polyethylene glycol (meth)acrylate, polyalkylene glycol (meth)acrylates, glycerin di(meth)acrylate and polyol (meth)acrylates.
  • These hydroxyl group-containing (meth)acrylates may be in the form of a single acrylate or a mixture of these acrylates.
  • Examples of commercially available products of the urethane poly(meth)acrylate include “UA-306H”, “UA-306T”, “UA-306I” and “UA-510H” all produced by Kyoeisha Chemical Co., Ltd., “KRM7864”, “KRM8452”, “EB1290”, “EB1290K” and “EB5129” all produced by Daicel Cytec Co., Ltd., “U-6HA”, “U-6LPA”, “U-15HA”, “UA-33H” and “UA-122P” all produced by Shin-Nakamura Chemical Co., Ltd., "UV7600B”, “UV7605B”, “UV7610B” and “UV7620EA” all produced by Nippon Synthetic Co.
  • the blending ratio (weight ratio) of the urethane poly(meth)acrylate and TAIC is usually 1:9 to 9:1 and preferably 1:1 to 1:4.
  • the crosslinking aid used in the present invention may contain a polyfunctional (meth)acrylate unless the effects of the present invention are adversely affected by addition thereof.
  • the polyfunctional (meth)acrylate is a compound having two or more (meth)acryloyl groups, and preferably three (meth)acryloyl groups, in a molecule thereof.
  • polyfunctional (meth)acrylate examples include trimethylolpropane tri(meth)acrylate, dimethylol propane tetra(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, and dipentaerythritol hexa (meth) acrylate.
  • the crosslinking aid used in the present invention may be used in either radiation-crosslinking or heat-crosslinking. That is, the resin composition obtained by blending the crosslinking aid with a cross-linkable polymer can be used either as a radiation-crosslinking resin composition or as a heat-crosslinking resin composition.
  • an ethylene copolymer is particularly preferred.
  • the ethylene copolymer is a copolymer of ethylene as a main component and a monomer copolymerizable with the ethylene.
  • the monomer include vinyl esters, unsaturated carboxylic acid esters, unsaturated carboxylic acids and metal salts thereof, unsaturated silicon compounds, and ⁇ -olefins.
  • polar monomers are preferred.
  • ethylene copolymer examples include ethylene-vinyl ester copolymers such as ethylene-vinyl acetate copolymers, ethylene-unsaturated carboxylic acid ester copolymers such as ethylene-methyl acrylate copolymers and ethylene-isobutyl acrylate-methacrylic acid copolymers, and ionomers thereof.
  • ethylene-vinyl ester copolymers such as ethylene-vinyl acetate copolymers, ethylene-unsaturated carboxylic acid ester copolymers such as ethylene-methyl acrylate copolymers and ethylene-isobutyl acrylate-methacrylic acid copolymers, and ionomers thereof.
  • ethylene-vinyl acetate copolymers particularly preferred are the ethylene-vinyl acetate copolymers.
  • the amount of the crosslinking aid of the invention compounded in the radiation-crosslinking resin composition or the heat-crosslinking resin composition is usually 0.1 to 3.0 parts by weight, and preferably 0.5 to 2.0 parts by weight based on 100 parts by weight of the ethylene copolymer.
  • the amount of the polyfunctional (meth)acrylate compounded is usually 0.1 to 3.0 parts by weight, and preferably 0.5 to 2.0 parts by weight based on 100 parts by weight of the ethylene copolymer.
  • a crosslinking agent is used together with the crosslinking aid.
  • an organic peroxide may be generally used.
  • the organic peroxide is not particularly limited as long as it is a known organic peroxide to generate peroxy radicals under the vulcanization conditions.
  • organic peroxide examples include di-t-butylperoxide, dicumylperoxide, 2,5-dimethyl-2,5-di(benzoylperoxy)hexane, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, t-butylperoxy-2-ethylhexyl-monocarbonate, 1,1-bis(t-butylperoxy)-3,5,5-trimethyl cyclohexane, 2,5-dimethylhexane-2,5-dihydroxyperoxide, t-butylcumylperoxide, ⁇ , ⁇ '-bis(t-butylperoxy)-p-diisopropyl benzene, 2,5-dimethyl-2,5-di(t-butylperoxy)hexyne-3, benzoylperoxide, and t-butylperoxy benzene.
  • the amount of the crosslinking agent compounded may vary depending on the type of the ethylene copolymer, and is usually 0.6 to 5 parts by weight, and preferably 1 to 2 parts by weight based on 100 parts by weight of the ethylene copolymer. In such a case as to carry out crosslinking by irradiation, the organic peroxide is not necessarily required.
  • optional additives such as reinforcing agents, fillers, plasticizers, processing aids, lubricants, pigments, anti-aging agents, coupling agents, ultraviolet absorbers and acid acceptors can be used.
  • anti-aging agents include dit-butyl-P-cresol, pentaerythrityl-tetraxy[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], 2,2'-methylenebis(2-methyl-6-t-butylphenyl), bis(2,2,6,6-tetramethyl-4-piperadyl)sebacate, N,N'-hexane-1,6-diylbis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionamide], bis(2,2,6,6-tetramethyl-4-piperadyl)sebacate, hydroquinone monomethyl ether, and methylhydroquinone.
  • the coupling agents include ⁇ -chloropropyl trimethoxysilane, vinyl triethoxysilane, vinyl-tris-( ⁇ -methoxyethoxy)silane, ⁇ -methacryloxypropyl trimethoxysilane, ⁇ -(3,4-ethoxy-cyclohexyl)ethyl trimethoxysilane, ⁇ -glycidoxypropyl trimethoxysilane, ⁇ -mercaptopropyltrimethoxysilane, ⁇ -aminopropyl trimethoxysilane, and N- ⁇ -(aminoethyl)- ⁇ -aminopropyl trimethoxysilane.
  • ultraviolet absorbers include 2-hydroxy-4-n-octyloxy benzophenone, 2,2-hydroxy 6-4,4-dimethoxy benzophenone, 2-(2'-hydroxy-5-methylphenyl)benzotriazole, and p-t-butylphenyl salicylate.
  • acid acceptors include magnesium hydroxide, calcium hydroxide, magnesium oxide, and zinc oxide.
  • the amount of the additives added is usually not more than 10 parts by weight, and preferably not more than 5 parts by weight based on 100 parts by weight of the ethylene copolymer.
  • the radiation used in the radiation-crosslinking accelerated electron beams, X-rays, ⁇ rays, ⁇ rays, ⁇ rays, and the like are available.
  • the irradiation dose may vary depending on the cross-linkable elastomer to be used, and is usually 0.1 to 500 kGy.
  • the heat-crosslinking is conducted by using a molding machine, for example, an injection molding machine, a compression molding machine and the like, and heating at a temperature of 150 to 200°C for about 2 to 30 min to obtain a molded body. If necessary, thereafter, the secondary crosslinking may be conducted by heating at a temperature of 150 to 200°C for 1 to 10 hr.
  • the crosslinking of the ethylene copolymer composition described above particularly the crosslinking using an organic peroxide is preferred.
  • the above ethylene copolymer composition is useful for use in the applications such as various packaging materials for foods, pharmaceuticals, industrial chemicals, and agricultural materials, various adhesive films, sealing films for various electric materials such as solar cells, liquid crystal, light emitting diodes, and organic EL, as well as useful for use in fields of hemodialysis, plasma component separation, desalting of protein solutions, fractionation, condensation, condensation of fruit juice, and wastewater treatment.
  • the above ethylene copolymer composition is useful as a sealing material used for assembly of various electronic material modules.
  • the sealing material in the case of a sealing material to be used in a considerably thickened form such as a sealing material for the solar cell, the sealing material fails to be cured with ultraviolet rays and electron beams, and therefore, the heat-crosslinking resin composition is used.
  • Respective components shown in Table 1 below were kneaded with an open roll mill.
  • EVA ethylene-vinyl acetate copolymer
  • TAIC produced by NIPPON KASEI CHEMICAL COMPANY LIMITED was used as crosslinking aid 1
  • respective compounds shown in Table 2 were used as crosslinking aid 2 in each Example or Comparative Example.
  • the resulting composition was subjected to hot press crosslinking (primary crosslinking) at 150°C to obtain a sheet having a thickness of 1mm.
  • a volume resistivity value of the sheet was measured by the method shown in Table 3. The measurement results are shown in Table 4.
  • a urethane poly(meth)acrylate was synthesized using isophorone diisocyanate as an organic isocyanate and pentaerythritol triacrylate as a hydroxyl group-containing (meth)acrylate.
  • the number-average molecular weight of the resulting urethane poly(meth)acrylate was measured by GPC. The measurement conditions are as follows.
  • An EVA sheet was produced using the above urethane poly(meth)acrylate as the crosslinking aid 2, and the volume resistivity of the EVA sheet was measured in the same manner as in Examples 1 to 3 and Comparative Examples 1 to 4.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Physics & Mathematics (AREA)
  • Electromagnetism (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Photovoltaic Devices (AREA)
  • Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
  • Sealing Material Composition (AREA)
EP14753580.1A 2013-02-21 2014-02-21 Crosslinking aid and practical application thereof Active EP2960291B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2013032282 2013-02-21
PCT/JP2014/054126 WO2014129573A1 (ja) 2013-02-21 2014-02-21 架橋助剤およびその応用

Publications (3)

Publication Number Publication Date
EP2960291A1 EP2960291A1 (en) 2015-12-30
EP2960291A4 EP2960291A4 (en) 2016-09-28
EP2960291B1 true EP2960291B1 (en) 2018-12-26

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Country Status (7)

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US (1) US9428672B2 (ko)
EP (1) EP2960291B1 (ko)
JP (1) JP5888466B2 (ko)
KR (1) KR102092570B1 (ko)
CN (1) CN105164198B (ko)
TW (1) TWI564342B (ko)
WO (1) WO2014129573A1 (ko)

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EP3034531A1 (de) 2014-12-19 2016-06-22 Evonik Degussa GmbH Dispersion zum einfachen Einsatz in der Herstellung von Verkapselungsfolien
EP3034529B1 (de) 2014-12-19 2017-06-14 Evonik Degussa GmbH Covernetzersysteme für verkapselungsfolien umfassend (meth)acrylamidverbindungen
EP3034525A1 (de) 2014-12-19 2016-06-22 Evonik Degussa GmbH Covernetzersysteme für Verkapselungsfolien umfassend Pentaerythritolverbindungen
EP3034568A1 (de) 2014-12-19 2016-06-22 Evonik Degussa GmbH Covernetzersysteme für Verkapselungsfolien umfassend Triallylisocyanurat und Triallylcyanurat
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EP3034530A1 (de) 2014-12-19 2016-06-22 Evonik Degussa GmbH Covernetzersysteme für Verkapselungsfolien umfassend Diene
EP3034526B1 (de) 2014-12-19 2017-06-14 Evonik Degussa GmbH Covernetzersysteme für Verkapselungsfolien
CN110050038A (zh) * 2017-01-10 2019-07-23 住友电工超效能高分子股份有限公司 交联树脂成型体、滑动构件、齿轮和轴承
KR101981331B1 (ko) * 2017-03-30 2019-05-22 에스케이씨에코솔루션즈(주) 태양전지용 봉지재 및 이를 포함하는 태양전지 모듈
JP7500457B2 (ja) 2020-07-30 2024-06-17 京セラ株式会社 太陽電池モジュール
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Publication number Publication date
CN105164198B (zh) 2017-05-31
JPWO2014129573A1 (ja) 2017-02-02
EP2960291A1 (en) 2015-12-30
JP5888466B2 (ja) 2016-03-22
TWI564342B (zh) 2017-01-01
US20150353784A1 (en) 2015-12-10
WO2014129573A1 (ja) 2014-08-28
CN105164198A (zh) 2015-12-16
TW201446877A (zh) 2014-12-16
KR102092570B1 (ko) 2020-03-24
KR20150119845A (ko) 2015-10-26
EP2960291A4 (en) 2016-09-28
US9428672B2 (en) 2016-08-30

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